A custom contemporary built in 1999 in the Kendall Estates section of Leominster sold for $1.57 million, the highest-priced home sale reported in the Worcester, Massachusetts metro area for the week ending August 16, 2026.
The week’s five highest-priced reported sales combined for $6.83 million, and each one landed in a different municipality: Leominster, Upton, Southborough, Westborough and Northborough.
The houses behind them date from 1985 to 1999 and run from a single-level contemporary on four acres in Northborough to a renovated Upton Colonial with a self-contained accessory dwelling attached by a breezeway.
No. 1 — $1,575,000 · 119 Olde Tavern Rd, Leominster, Massachusetts
A custom contemporary at 119 Olde Tavern Rd, in the Kendall Estates section of Leominster, sold for $1,575,000 on August 12, 2026, the highest reported price anywhere in the metro area that week. The house was built in 1999 and is recorded at five bedrooms, eight bathrooms and a reported 4,750 square feet.
Listing materials describe an open plan in which a large sunken wet bar opens to the dining room and to a living room with a nine-foot marble fireplace surround under a soaring ceiling, with multiple sliders leading out to a private rear yard. The kitchen is fitted with high-end appliances, and a first-floor office that can double as a bedroom sits beside a dedicated laundry room. The primary suite is also on the first floor, with its own fireplace, multiple closets and a private bath.
Upstairs are two more bedrooms, each with a private bathroom, plus a further room set up as a bedroom, family room or gym. The lower level is finished as a media room and game room with an additional room and two more full baths.
Laurie Howe Bourgeois of Coldwell Banker Realty – Leominster was the listing agent. Bourgeois represented the listing side of the highest-priced home sale reported in the Worcester, Massachusetts metro area for the week ending August 16, 2026, a transaction that went under contract the same day the current listing went live and closed at its full asking price. The property previously changed hands for $685,000 in 2021. Stephen Fraticelli of Karen Packard Real Estate Inc. represented the buyer.
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No. 2 — $1,375,000 · 8 Stearns Rd, Upton, Massachusetts
A Colonial at 8 Stearns Rd, at the end of a private cul-de-sac on nearly two acres in Upton, changed hands for $1,375,000 in a closing dated August 10, 2026, the second-highest reported price of the week. Built in 1985 and renovated since, it is recorded at five bedrooms, five bathrooms and a reported 4,395 square feet across a main house and a fully equipped accessory dwelling.
The main house has two fireplaced living rooms, a mahogany deck and a kitchen with quartz countertops, double wall ovens, a gas cooktop and an oversized butcher-block island. A new great room sits above the garage, and four bedrooms are on the second floor, among them a primary suite with a walk-in closet. A breezeway connects the self-contained accessory dwelling, which has its own full kitchen, fireplaced living room, office and bedroom.
Kathleen Nicoloro of Ferrari + Co. Real Estate was the listing agent. The house went under contract 22 days after the current listing date, and the closing ranked No. 2 in RealtyWire’s Worcester Metro Area Top 5 for the week. The property previously changed hands for $715,000 in 2022. Martha Celli of Laer Realty Partners represented the buyer.
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No. 3 — $1,333,000 · 39 Darlene Dr, Southborough, Massachusetts
39 Darlene Dr, a custom-built Southborough house dating to 1994, sold for $1,333,000 on August 14, 2026. It is recorded at three bedrooms, four bathrooms and a reported 3,576 square feet.
A full kitchen renovation brought in Wood-Mode cabinetry, marble countertops, an expansive island, two dishwashers and double wall ovens, open to a front-to-back family room with a fireplace. Four rooms with closets sit off an open second-floor hallway, among them an ensuite primary bedroom with a separate dressing room, and the walkout lower level is fitted with a wet bar and a full bath. Outdoors there is a fire pit and an expansive patio, and recent work includes exterior painting in 2025 and a 30-year shingle roof in 2016.
Lisa Pezzoni and Benjamin Montenegro of Andrew J. Abu Inc., Realtors® were the listing agents. Their listing went under contract 4 days after the current listing date, and the sale ranked No. 3 among home sales reported across the Worcester metro area that week. The property previously changed hands for $85,000 in 1994, the year it was built. Chelsea Eaton of Lamacchia Realty, Inc. represented the buyer.
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No. 4 — $1,290,000 · 191 Ruggles St, Westborough, Massachusetts
In Westborough, a 1987 residence at 191 Ruggles St on 1.25 acres traded for $1,290,000 in an August 11, 2026 closing, the fourth-highest reported price of the week. It is recorded at four bedrooms, five bathrooms and a reported 4,480 square feet.
Wide-plank oak flooring runs through the house, and the kitchen holds Miele appliances, double ovens, a built-in espresso maker, a proofing oven and a quartz-topped center island. The first-floor primary suite has radiant heated floors and a tiled shower, and a second primary suite, a home office and a bonus room fill out the plan. The grounds carry extensive masonry, a labyrinth meditation path, a built-in fireplace with seating and a heated and air-conditioned outbuilding usable as a studio, office or fitness room.
Mary G. Wood of Lamacchia Realty, Inc. was the listing agent. The $1,290,000 closing put Wood on the listing side of the No. 4 sale in RealtyWire’s Worcester Metro Area Top 5 for the week ending August 16, 2026. The property previously changed hands for $282,500 in 1990. Gina B. Lewis of ERA Key Realty Services – Worcester represented the buyer.
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No. 5 — $1,252,500 · 347 Green St, Northborough, Massachusetts
A single-level contemporary at 347 Green St in Northborough, on a manicured four-acre parcel ringed by mature trees, sold for $1,252,500, with the closing recorded August 11, 2026. Built in 1987, the house carries four bedrooms, three bathrooms and a reported 3,693 square feet.
The sun-filled plan takes in exposed brick accents, fireplaces and maple hardwood floors, with a custom white kitchen finished in granite and a four-season sunroom facing the trees. An outbuilding offers flexible room for a home office, studio or workshop, and the property carries debt-free solar panels, an EV charger and a recently updated heating and cooling system.
Tony Mallozzi of Anthony Joseph Real Estate LLC was the listing agent. The house went under contract 8 days after the current listing date, and it closed as the No. 5 transaction in RealtyWire’s Top 5 reported home sales for the Worcester, Massachusetts metro area for the week ending August 16, 2026. The property previously changed hands for $747,500 in 2015. Jeanne Burton of Barrett Sotheby’s International Realty represented the buyer.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, August 16, 2026. The report may exclude private, off-market, delayed or nondisclosed transactions. Prices, property details and professional representation are reported as available at publication and may be updated following confirmation from transaction participants.
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